- And You Thought It Would Fail: Hugh Grant confessed that during filming, he thought the movie was awful.
- Base-Breaking Character: Carrie. Some find her charming and mysterious, others aren't very impressed with her basically dragging Charles along, while marrying another man.
- Designated Hero: Carrie cheats on her fiancé twice and Charles ditches his girlfriend at the altar, but we're supposed to root for them to get together.
- Designated Villain: It seems that the writers had Charles reconcile with his least favorite ex, the shrewish Henrietta, because he would have looked like a jerk dumping any of the nicer ones or Fiona.
- Even worse, she's actually quite nice at the third wedding, apologizing for how she acted at the second one. Presumably, this is why he decided to give their relationship another try, so he ends up looking like a jerk anyway.
- Even her behavior at the second wedding is unfairly maligned. Yes, she's all weepy and teary, but that's hardly an uncommon reaction for someone running into an ex.
- Fair for Its Day: As eyebrow-raising as the Bury Your Gays funeral of the title is, the film was incredibly ahead of its time in presenting a gay couple as a completely accepted part of a large group of otherwise straight friends, whose relationship is just as valid as any of the others—and is looked at as an inspiration for the others, with Charles openly stating, "If we can't be like them, what's the point?"—and the death of one being a tragedy which is in no way played for laughs.
- Given the above, that hardly seems to call for raised eyebrows.
- "Funny Aneurysm" Moment: Carrie says that she's slept with fewer men than Madonna but more than Princess Di, a joke that seems much more awkward after Princess Diana's death in 1997.
- Heartwarming Moments:
- David's girlfriend's tentative attempts to speak to him in sign language, and his smile.
- After Charles bails out of marrying Henrietta and is feeling terrible about it, and the others aren't exactly impressed with him, Tom pipes up that if he really wasn't sure about marrying her, then he was right not to go through with it. Fiona, who throughout the film has been responding to all Tom's remarks with an irritated "Bugger off, Tom", looks as though she's about to say it again — then she just touches him on the shoulder and says gently, "Quite right, Tom."
- Hilarious in Hindsight: Fiona claims to have once been a lesbian for just fifteen minutes. The Red Nose Day sequel reveals her daughter is a lesbian...and gets married to Charles' daughter!
- Memetic Mutation: To this day, "# Of _______ And A _______" or even just "# Of_______" is recognizable as a play on this movie's title.
- Narm: Andie McDowell doesn't exactly give the most electrifying performance of her career here. Especially "Is it still raining? I hadn't noticed."
- One-Scene Wonder: Rowan Atkinson as the newly appointed priest at wedding two.
- Relationship Writing Fumble: A sizable number of fans wish Charles had ended up with Fiona, after the moving scene where she reveals to him that she's loved him since they first met. The 2019 Red Nose Day sequel makes up for it by revealing that their daughters end up together.
- Retroactive Recognition:
- Nicola Walker of Unforgotten is half of the "dreadful folk duo" at the first wedding.
- An example involving someone who became famous in a different field: Amber Rudd is credited as "Aristocracy Co-ordinator" and also briefly appears as an extra, some years before going into politics and rising to the post of Home Secretary.
- Strangled by the Red String:
- Charles declares his love for Carrie at their third meeting when they've only slept together twice and haven't even seen or spoken to each other in the months between the three incidents. Then, despite sufficient time to get over his feelings, he ditches his fianceé at the altar to get together with her. They have a grand total of five meetings in the film, but this is supposedly enough for them to decide they want to spend the rest of their lives together. To his credit, he does cite how ludicrous it is when he tells her he loves her and when he "proposes", he outright says that they need to spend time getting to know each other.
- Bernard and Lydia are married within three months of hooking up at the first wedding, though this is tempered by the fact that they've at least known each other for years even if they haven't been dating.
- Tear Jerker: Matthew reading W.H. Auden's "Funeral Blues" at the funeral.
- Unintentionally Sympathetic: Yes, Henrietta's nuts, but she didn't deserve to literally be left at the altar like that.
YMMV / Four Weddings and a Funeral